Shums Kassam

Excited to back the incredible team at peel ai (revtech startup). I don't do a lot of early stage investing, but a few things got me over the finish line here. I looked at typical early stage investment criteria like: the founding team’s domain expertise (deep); TAM (large); early customer traction (yes), and so on. Lots of people do that. I’m really more interested in unconventional criteria. Things that other investors may not pay attention to. With Peel, I found some things I really liked: - The product is unique. In fact, when I tell people what Peel does, most people say, “Really? That works?” That’s a great sign and yes, it does work. - Peel has an opportunity to go-to-market via a channel that is not very well known/uncrowded. That is hard to find these days and they found it. - I really like startups where there are logical “intermediate” exits available. In other words, you don’t have to do a massive IPO to be successful. I think that’s good for founders and can be good for investors who aren’t getting tsunami’d by AUM. That’s the case here. - I like companies where I can add value on day one. Peel is in the revtech space, an area I know fairly well based on my experience at TOPO. - Trust is a big deal at an early stage startup that’s taking on its first investors. Basically the company doesn’t have a track record, but wants a bunch of money. You can’t get there as an investor unless you trust the team. The founding team has deep expertise, a strong work ethic, etc. But most importantly, I just trust them. Anyway, I’m into these unconventional investment criteria. It’s just a great way to avoid what has become a crowded investment space (early stage startups) and help founders who are building unique companies. Thanks Brannon Santos and Ben Henson - looking forward to working together! 🤓 📢 BTW, right now, Peel is focused on getting product feedback. If you’re open to helping us out with that, please let me know!

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My 7-year journey via Maple VC with Clay. Thanks Josh Scott at BetaKit for covering the story. I was first introduced to Kareem Amin through a fellow Canadian expat and now Maple founder, Michael Hershfield of Accrue Savings. They first met working at Sailthru in NYC where Kareem sold his first company. In 2016, Kareem started to tinker on new ideas with his cofounder Nicolae Rusan and I was fortunate to meet them at this time. This happened to align with me establishing Maple 1 in November 2016 on the simple thesis of backing Canadians building in America. We noticed that Canadian expats, who graduate from Canadian universities, go on to build some of the biggest companies in tech – Uber, Slack, Instacart, Notion, Faire, Databricks, Cloudflare, Roblox and most recently, OpenAI. Kareem and Nicolae seemed to match this pattern as two graduates from McGill University building in the US. In 2017, they landed on a very clear mission to make programming accessible to all. They painted a picture of replacing the black terminal that developers use, with a spreadsheet that is connected to the internet which could allow non-developers to automate work. What we saw immediately that gave us conviction was a very big ambition (making programming accessible to all) with a unique insight (using a spreadsheet) via a new method of no-code tooling. This reminded us of the early days at Uber: The promise to deliver you anything (big ambition) by starting with a black car that takes you from point A to point B (unique insight) via your phone (new method). We first committed to investing in Clay in Jan 2017 before the company had a lead. In June 2017, we were thrilled to learn that First Round Capital was going to lead their Seed. Sequoia Capital led the Series A in June 2019, which was surprising, since we had no revenue and were still figuring things out. However, the low-code no-code category was starting to take off. Then, they spent the next 3 years figuring out where to focus. During this phase it was fascinating to witness the many disbelievers. We had folks tell us that we should mark this investment to $0. In late 2021, they decided to narrowly focus on automating sales and this turned out to be the big unlock. Varun Anand joined as a cofounder leading their GTM efforts. The timing played out beautifully with new LLMs that we could use to automate growth in a way that hadn’t been done before. Clay relaunched in Feb 2022 with $0 in revenue and has not looked back since. We 10x’d two years in a row, all organically, achieving 100k users, 2500+ customers, and 11k people exchanging ideas in our Slack community. Maple has tripled down since the Seed through the Series B which was just led by Meritech Capital. We have a strong feeling that Clay has a real shot at realizing that vision they first shared with us 7 years ago.

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We've seen this so many times. Your brand/customers/product is unique, but that doesn't mean you should reinvent the wheel with your commerce/marketing stack experience. When brands choose heavily-customized tech stacks, it usually leads to high implementation & maintenance costs. But more importantly, it makes it difficult to iterate down the line. You'll be stuck with your "custom" ecom site, loyalty program, unique UX for years - while your competitors will blow past you with "out of the box" tools.

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Collision Conf is one of the biggest tech+AI events in North America and I am looking forward to learning more in this exploding space. If anyone is heading that way, feel free to ping and we can connect! #AI #generativeAI #digitaltransformation

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Too often, we get caught up in pursuing perfect outcomes, forgetting that innovation is a journey of trial and error. Check out my full Dialog interview with Mourad Zerroug, CTO at Splash (SplashThat.com): https://lnkd.in/eMgEyBt9

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Spent a wonderful week in Canada with family! Now back to business.. Here's your weekly AI update: 🔙 𝐓𝐡𝐞 𝐁𝐚𝐜𝐤𝐰𝐚𝐫𝐝 𝐏𝐚𝐬𝐬: 𝐑𝐞𝐯𝐞𝐫𝐬𝐢𝐧𝐠 𝐓𝐡𝐫𝐨𝐮𝐠𝐡 𝐭𝐡𝐞 𝐀𝐈 𝐖𝐞𝐞𝐤 Week 51 | August 5 - August 11 The OpenAI Brain Drain Industry: 🚨OpenAI co-founder John Schulman leaves for Anthropic; President Greg Brockman is taking extended leave through the end of year. What's interesting is that three of their most technical co-founders (Ilya Sutskever, John Schulman, Andrej Karpathy) have all left the company now. This then begs the question - is this a result of natural silicon-valley attrition, or is there something deeper going on here? And moreover, how will this impact the technical moat that OpenAI has built over the years? (https://lnkd.in/gztRKhwV) 🚨Google announced that new Gemini AI-powered features will be incorporated in a variety of home devices, such as Google Home and Nest (https://lnkd.in/gV2QacAQ?). It also announced a significant reduction in token cost of Gemini 1.5 Flash (https://lnkd.in/gbNe6yNU?) 🚨Figure releases Figure 02, it's newest humanoid robot. Figure has been actively testing robots with BMW at a manufacturing plant. Figure last raised $675M Series B in February 2024, valuing the company at $2.6 billion. (https://lnkd.in/gZnPSke4) 🚨Mark Zuckerberg said on Meta's Q2 earning call that to train Llama 4, the company will need 10x more compute than what was needed to train Llama 3. (https://lnkd.in/g5pEPrTw?) 🚨Elon Musk filed a lawsuit against Sam Altman and Greg Brockman, renewing claims that the company is betraying its founding aims of benefiting the public good rather than pursuing profits. (https://lnkd.in/gAk5grU6) Financing and M&A: 🚨Groq raises $640m in Series D at a $2.8B valuation. The round was led by Blackrock Private Equity Partners with participation from other investors such as Neuberger Berman, Type One Ventures, Cisco, KDDI, and Samsung Catalyst Fund. (https://lnkd.in/gRtKQKvW?) 🚨Hugging Face acquires Seattle data storage startup Xethub. The HF team plans to integrate Xethub's backend storage technology, enabling developers to host more large models and datasets than currently possible. CEO Clem Delangue 🤗 confirmed this was the largest acquisition the company has made thus far. (https://lnkd.in/g8fJ-BjT) 🚨OpenAI is leading a $60m Series B funding round for Opal Camera, a maker of professional-grade webcams(https://lnkd.in/gMT9dkTG) 🚨ProRata.ai a company that has invented an attribution technology to properly compensate content owners, has raised a $25m Series A, led by Prime Movers Lab, Mayfield Fund and Revolution Ventures. (https://lnkd.in/gumjbWmj) R&D: 🚨Alibaba Group releases Qwen2-math, a SOTA model for math-specific tasks. (https://lnkd.in/g8Jh3M7T?) Other Interesting Resources: 🚨 Between May and August, more Humane AI Pins were returned than purchased (https://lnkd.in/gy56qpKm?). 😯

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In #uWaterloo, We sat around a table, And asked each other to think of #startup ideas I chimed in, "Let's just make a dollar" Thinking that was a good start. We thought of outlandish ideas Crazy things that others had already done But we never made that dollar Turns out startups aren't about flash That new thing, Crazy idea It's about money. Can you make that dollar? Can you actually sell a product or a service? We just crossed 1000 payments processed. #ZeroInbox crossed 1000 payments. I'm flabbergasted. How did I go from struggling to make a single dollar To processing thousands? I started out this journey wanting to be an entrepreneur. Like anything it took time, and hard work. Some crazy crazy luck, and really really nice people. I made my first dollar not through #zeroinbox But through Facebook Marketplace! Selling gold I brought from a country I'd rather not name. Start with a dollar. A penny. #Startsomewhere, #startsomething!

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If I was an A player / high performer seeking employment right now, I'd look for jobs at organizations running one of these business operating systems: Scaling Up: A Gazelles Company, Metronomics, or EOS - Entrepreneurial Operating System. There are several reasons for this: -Core Values-Driven CEOs: Many will have CEOs that actually live their company core values (and insist everyone else does, too), giving you the best chance possible to thrive -A Player Team: Because these organizations are more likely to use Topgrading to hire, you'd be part of a drama-free, A Player team (do not underestimate the importance of this; if you've had bad team members or have been dismayed by workplace drama, you understand) -Get Paid More: Compensation will likely be at the high end for your role because these organizations understand the value the A Player creates -5D Focused Leadership Teams: Leadership teams are focused on Overcoming the Five Dysfunctions of a Team, resulting in less workplace politics (doing the wrong thing for the wrong reason) and way less stupidity from leaders All of these things will result in the most fulfilling working environment you've ever had. Remember the "Great resignation"? That may as well have been a myth to my clients. Why? Nobody leaves an A player team. NOBODY. That was a problem for companies that don't live there core values and that tolerate B and C players. Unfortunately, there isn't a public list of these companies. That would be one incredible A Player recruitment website. But there are a few things A players can do to find these employers: 1. Reach out to the organizations above to find out if they know of companies in your area using their systems/tools 2. Reach out to your local chapter of Entrepreneurs' Organization or Young Presidents' Organization - that's where the self-aware leaders using these systems/tools congregate ***Important interview question all candidates for all candidates to ask: Is your CEO a member of EO or YPO? Self-aware leaders tend to join these peer learning associations, and that's the kind of leader you generally want as an employer/leader.*** 3. Reach out to Metronomics, Scaling Up, or EOS coaches in your area to find out which of their clients is currently hiring. I'll be posting some of my clients' open positions - as well as background on the company - here in the near future. Find a company that is deserving of your behavior and talents. #Metronomics #ScalingUp #EOS #Hiring #JobSeekers #Jobsearch #employerofchoice #topgrading #fivedysfunctionsofateam #corevalues #YPO #EO #Grovertalent #talent #Aplayers #Aplayerhiring

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Hi friends, I'm looking for your recommendations for a startup bookkeeper & accountant - noting that I now own a Delaware (U.S.) company, a B.C (Canadian) one, and soon an overseas one and they each interact with each other. It seems like I need a unique one in each region to understand the nuances in each region, which is fine if that's the best option, but as they don't seem to know the rules in the other regions, so I don't get the best tax planning advice as a result for the various pass through options. Surely there's a better option than the big 4, for startups? (Seems like a startup idea in itself)

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Just had to share this gem from Collision Conf in #Toronto. Among the #startups and VCs, I spotted a guy with a shirt saying, "Ask me about my CAC." Naturally, I asked. Sebastian Fallenbüchl, BASc., the wearer, shot back, "My CAC is getting lower as you just approached me." Genius. Seb’s witty remark was more than just a laugh — it was a reminder that business is about people. Metrics like CAC are crucial, but so are the connections and conversations that drive them down. Takeaway? Be #approachable. Humor and humanity can make all the difference. Thanks for the insight and the laugh, Seb. Here’s to more moments like these! #Networking #BusinessInsights

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Sidewalk Labs (Part of Google), another showcase of Canadian politicians bending over for a big US corp, with ZERO tangible results 💩 Roxana and I attended a "private investor demo" session in 2019. A block of wood was passed among the audience, supposedly the NEXT BIG BREAKTHROUGH in urban development! Demo concluded, by observing a piece of wood! Building blocks of future skyscrapers! The promise? With this, Google will build a "Smart City" for us, the peasants of Toronto, in Queens Quay 🏖️🏢 Sidewalk Labs' website now points to a newer Google scam, it reads: "Build Sustainably with Google Earth"! Bait and switch, but let enough time pass so no one remembers 🤢 https://lnkd.in/gd3B-a6m Guess now the investors and Ontario Government | Gouvernement de l’Ontario have shit loads of these wooden blocks, ready to shove up somewhere, to find a use for! All because the name "Bloomberg" sounds authoritative enough to our ears? Surely that's capital well spent, instead of investing in local talent! 🤔 Will Canada's tech ecosystem ever crawl out of Silicon Valley's shadow, and stand on its own? ⌚👀⛔

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Who better to talk about Shopify's trajectory and future than Benjamin Lang • OLY.? In our 50th podcast episode, I had an extremely interesting conversation with Benjamin about a lot of awesome topics that are close to my heart, and I can't be more excited about what's happening in the Shopify ecosystem. For example: • B2B features • From only online commerce to commerce in the more broad sense of the word • The focus on TCO • Customer centricity I'm very grateful I had the chance to talk to Benjamin, and I hope we can do it again some time in the near future as things are moving so fast. Thanks a lot for your time and effort Benjamin! #deardigital #shopify #podcast

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Toronto Startup Guide for Founders. Thank you Yoran Beisher and Michael Liu for pulling this map together and for keeping it up to date 🙌 #CommunityBuilders Now, who can do this and update the old Montreal Startup Guide for Founders?

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Today at Antler VC Toronto, we had Michael Kravshik, CPA, CA, the founder of LumiQ come speak to us. The cohort is in week 5 of the 10-week residency. We’re still very much in the process of solidifying our cofounders and searching for product market fit. So Michael’s speech was timely, informative, and inspirational. Here were my key take-aways. 𝐎𝐧 𝐟𝐢𝐧𝐝𝐢𝐧𝐠 𝐩𝐫𝐨𝐝𝐮𝐜𝐭 𝐦𝐚𝐫𝐤𝐞𝐭 𝐟𝐢𝐭  🔸 Ideas don’t matter, the iterative test approach does; it’s more painful in the present but saves you lots of time in the future 🔸 Start with really broad assumptions, start validating those broad ideas, and then through the process of speaking to customers to get to the really narrow concepts 🔸 At one point Michael and his co-founder went through invalidating 25 ideas, which would seem discouraging but they grew and developed a lot through this process (even though they didn’t know it at the time) 🔸 At one point they did a mind-boggling 500 one-on-one interviews in the span of 6 weeks 🔸 The only sustainable advantage you can in a startup is knowing your customer better than anyone else 🔸 PMF is a moving target 🔸 PMF is treated as a verb at LumiQ 𝐀𝐝𝐯𝐢𝐜𝐞 𝐅𝐨𝐫 𝐅𝐨𝐮𝐧𝐝𝐞𝐫𝐬 🔸 Be curious, open-minded, and be willing to kill your babies 🔸 If you keep going, you will eventually create your own luck 🔸 Lots of people get stuck in sunk-cost fallacy land, but you should listen to your gut and pivot when it doesn’t feel right 🔸 Founders have a reputation for being like cockroaches, and rightfully so, shamelessness can take one quite far I also asked Michael during the QA on what his emotionally compelling reason was for overcoming so many challenges to get the company to where it is today, and his answer was really insightful and relatable. He said that 𝐛𝐞𝐢𝐧𝐠 𝐚 𝐟𝐨𝐮𝐧𝐝𝐞𝐫 𝐢𝐬 𝐚 𝐥𝐢𝐟𝐞𝐬𝐭𝐲𝐥𝐞 𝐜𝐡𝐨𝐢𝐜𝐞, 𝐧𝐨𝐭 𝐚 𝐜𝐚𝐫𝐞𝐞𝐫 𝐜𝐡𝐨𝐢𝐜𝐞. Furthermore, if you’re not crazy AND stupid you probably shouldn’t do this! Thanks for bestowing your wisdom on us Michael Kravshik, CPA, CA and I hope I captured your words and sentiments correctly! 😃 #startups

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"Entrepreneurship is painful and sometimes rewarding." This quote naturally came out during a check-in call with my good friend and fellow entrepreneur, Gilad, who is building a great product at Sequence (I just wish they were available in Canada) 😢 As soon as I said it, both Gilad and I reflected on how true that statement is in describing the journey of building something. Shoutout to all the business owners and entrepreneurs out there taking the pain with a pinch of reward. #startupjourney #pain #entrepreneurship #grit

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I’d like to extend a huge thank you to the Google Cloud team for inviting me to join the panel at their “AI Startup Trailblazers” event in Toronto last week. ICYMI; here’s what I shared. 🤝 Mantle's approach to leveraging AI is simple: we want AI to assist our end users’ workflows rather than replace them. 🕒 Mantle has disrupted the cap table management space by utilizing LLMs, slimming down the onboarding and document processing time from what would traditionally take weeks to minutes. ✅ Not only does this greatly increase the trust that the data you see in-platform up-to-date and accurate, but it also enables a next-generation in terms of customer experience. If you're interested in learning more, I published an article with Google where we dive more into Mantle’s AI-driven document integration. You can check it out here: https://lnkd.in/gKNzum_6 Big shoutout to Alison Drader Nida Khan Michael Huang Stephan Bitton for being awesome hosts and running an amazing event!

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I stayed up coding until 4am so many nights for two years when I started Lightspeed Commerce — to me, this is part of the entrepreneur journey. Had a blast reflecting on those early years and discussing the challenges and opportunities of navigating a tech startup with Harry Stebbings from 20VC. Some takeaways: - Achieving strong product-market fit requires an iterative, customer-centric approach — especially with early users. Lightspeed wouldn’t have achieved profitability if we weren’t so close to our customers. - Companies can take different paths to scale, each with its trade-offs — some bootstrap profitably for years before taking VC funding. Sometimes you need the slow-burn process to create something truly phenomenal. - Founders must be willing to adapt their sales and distribution strategies as the business matures, especially after going public. If you’re a founder or entrepreneur, I think this episode will provide lots of value. Thank you to Harry and the team at 20VC for having me. Links to the interview in the comments 👇

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I rarely share podcast episodes here. But this one is a MUST listen to both INVESTORS and founders operating in bricks&mortar hospitality & retail technology. So many true, real, no BS points Dax Harry Stebbings. 👏🏼 Be bold enough to operate with a sales strategy and approach that many VCs won’t understand or approve but that works wonders in that space and builds this amazing, sticky, powerful model that most platforms in the space can’t crack or are afraid to (because it doesn’t tick some boxes you read/hear about from the tech/VC experts) 🚀 A growth trajectory that changes and originally is not on the typical VC path but then, once the “cockroach”, groundwork is done you’re in an exciting and unique position to scale with a product market fit that’s hard to beat - PMF and growth not achieved due to endless millions raised but a real PMF that makes thing sticky, powering your product-led growth 👊🏼 Stay super close to your customers. No matter how big you become, but especially in the first 5-10 years literally speak to them DAILY. Not many manage to make it work for hospitality or retail SMEs, it’s one of the hardest group to find PMF with. But once you nail it - you’re like a constantly growing massive mountain 🏔️ - sky is limit & no one can’t move you no matter what. Don’t build businesses to please an investor’s thesis/POV which you’re currently talking to or following on LinkedIn. Build a business together with your ICP customers and bring them the most value you possibly can. The rest will follow. Even the ticked boxes that you read so much about.

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There goes another unstressed 🧘 month building atono... We are four months in to building in public, so some updates to share: 🇨🇦 People: 13 co-founder-employees based in Western Canada, eh 🥳 Culture: v1.0 covering our Principles, tenants and game rules, check ✏️ Design: Research and focus groups complete. Roadmap to MVP complete.  Mocks built through May. Looking into customer forums next (slack or reddit?) 🏗️ Build: MVP level provisioning, users, teams, roles & permissions with automated testing. Now we're building the fun stuff: stories, backlogs, bugs, slack integration and other goodies 🛒 Marketing: Tone & voice guide, v1 ICP, v1 Buyer's Journey (scaffolding and tooling needed), pricing, packaging and legals - now starting on our website, oh yeah mustn't forget that 💰 Other stuff: Closed our Seed Round 🙌, implemented an accounting system, bank accounts, corp filings, health ins, payroll, etc. Being cash-careful and stretching

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